Cesium carbonate → 4-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide

HRID 1011540Notes

Reaction equation

HRID 1011540 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[CH2:19][OH:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:28][C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)[C@@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[CH2:19][OH:20])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 869964-(Bromomethyl)benzonitrileHCID 59497810HCID 59497810, compound

Product 1

HCID 666696104-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (126 mg, 0.39 mmol), cesium carbonate (254 mg, 0.78 mmol), and 4-(bromomethyl)benzonitrile (92 mg, 0.47 mmol) was stirred in 2 mL dimethylformamide for 1.5 h. The reaction was partitioned between 25 mL diethyl ether and 25 mL 0.1 M HCl, concentrated and purified by flash chromatography on 40 g silica gel with 0 to 70% ethyl acetate in hexane to yield 4-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (152 mg, 90%). 1H NMR (400 MHz, CDCl3) δ ppm 7.73 (2H, d, J=8.31 Hz), 7.60-7.65 (2H, m), 7.54 (2H, d, J=8.31 Hz), 7.50 (2H, d, J=8.56 Hz), 4.65 (1H, d, J=16.12 Hz), 4.01 (1H, d, J=16.12 Hz), 3.76-3.88 (1H, m), 3.61-3.72 (1H, m), 3.28-3.41 (1H, m), 2.18 (1H, br. s.), 1.44-1.63 (5H, m), 1.11-1.40 (6H, m). LC/MS R.T.=2.76 min; [M+H]+=433.14. HRMS [M+H]+ calc'd 433.1353, found 433.1352.

Workup

  1. customThe reaction was partitioned between 25 mL diethyl ether and 25 mL 0.1 M HCl
  2. concentrationconcentrated
  3. custompurified by flash chromatography on 40 g silica gel with 0 to 70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-51e2acc0951244efb17eef1d193707d1
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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